
%0 Journal Article
%A Bergamasco, R 
%A Horn, DHS 
%A Nearn, RH 
%A Wilkie, JS 
%T Insect Moulting Hormones. LV. Experiments Directed Towards the Synthesis of Non-steroidal Ecdysone Analogues
%J Australian Journal of Chemistry
%D 1985/03/01
%V 38
%N 3
%P 475-483
%K 
%R https://doi.org/10.1071/CH9850475
%U https://www.publish.csiro.au/paper/CH9850475 
%X Exploratory studies aimed at the synthesis of the non-steroidal ecdysone analogue (4aR,7S,8aR,-1&#8242;RS,4&#8242;R)-7-hydroxy-3-(1&#8242;-hydroxy-4&#8242;,8&#8242;- dimethylnonyl )-4a-methyl-4a,5,6,7,8,8a-hexahydronaphthal-en- 1(4H)-one (3) have led to in efficient method of joining the cyclic and side-chain synthons by reacting the vinylogous ester (4a) with 1-lithio-4,8-dimethyl-1,1-bis( methylthio ) nonane (12) to yield (4&#8242;RS)-3- [4&#8242;,8&#8242;-dimethyl-1&#8242;,1&#8242;-bis( methylthio ) nonyl ]-5,5-dimethylcyclohex-2-en-1-one (13). This thioacetal on reaction with boron trifluoride  etherate and mercuric oxide afforded, quantitatively, the diketone (4&#8242;RS)-3-(4&#8242;,8&#8242;-dimethyl-1&#8242;-oxononyl)-5,5-dimethylcyclohex-2-en-1-one (14) which was selectively reduced in 85% yield to the required model compound (4&#8242;RS)-3-(1&#8242;-hydroxy-4&#8242;,8&#8242;-dimethylnonyl)-5,5-dimethylcyclohex-2-en-1-one (15). 
